HUT62560A - Process for producing 24-oxa derivatives belonging to vitamin d series and pharmaceutical compositions comprising same as active ingredient - Google Patents

Process for producing 24-oxa derivatives belonging to vitamin d series and pharmaceutical compositions comprising same as active ingredient Download PDF

Info

Publication number: HUT62560A
Authority: HU; Hungary
Prior art keywords: oxa; formula; hydrogen; dihydroxy; compound
Prior art date: 1990-04-06

Application number

HU923157A

Other languages

English (en)

Hungarian (hu)

Inventor

Guenter Neef

Gerald Kirsch

Andreas Steinmeyer

Katica Schwarz

Matthias Braeutigam

Ruth Thieroff-Ekerdt

Petra Rach

Original Assignee

Schering Ag

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1990-04-06

Filing date

1991-04-08

Publication date

1993-05-28

1991-04-08 Application filed by Schering Ag filed Critical Schering Ag

1992-12-28 Publication of HU9203157D0 publication Critical patent/HU9203157D0/hu

1993-05-28 Publication of HUT62560A publication Critical patent/HUT62560A/hu

Links

239000008194 pharmaceutical composition Substances 0.000 title claims description 8
229940046008 vitamin d Drugs 0.000 title claims description 7
238000000034 method Methods 0.000 title claims description 4
239000004480 active ingredient Substances 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 37
229910052739 hydrogen Inorganic materials 0.000 claims description 14
239000001257 hydrogen Substances 0.000 claims description 14
239000011647 vitamin D3 Substances 0.000 claims description 10
229940021056 vitamin d3 Drugs 0.000 claims description 10
125000000217 alkyl group Chemical group 0.000 claims description 9
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 7
235000019166 vitamin D Nutrition 0.000 claims description 7
239000011710 vitamin D Substances 0.000 claims description 7
150000003710 vitamin D derivatives Chemical class 0.000 claims description 7
229930003316 Vitamin D Natural products 0.000 claims description 6
QYSXJUFSXHHAJI-XFEUOLMDSA-N Vitamin D3 Natural products C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C/C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-XFEUOLMDSA-N 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
125000002252 acyl group Chemical group 0.000 claims description 5
125000006239 protecting group Chemical group 0.000 claims description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
230000032050 esterification Effects 0.000 claims description 3
238000005886 esterification reaction Methods 0.000 claims description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
150000003855 acyl compounds Chemical class 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
-1 open Chemical group 0.000 description 17
239000000243 solution Substances 0.000 description 14
239000000203 mixture Substances 0.000 description 13
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
229960005084 calcitriol Drugs 0.000 description 9
239000011612 calcitriol Substances 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 6
GMRQFYUYWCNGIN-NKMMMXOESA-N calcitriol Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@@H](CCCC(C)(C)O)C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C GMRQFYUYWCNGIN-NKMMMXOESA-N 0.000 description 6
235000020964 calcitriol Nutrition 0.000 description 6
230000000694 effects Effects 0.000 description 6
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 6
238000012360 testing method Methods 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
239000012230 colorless oil Substances 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
229910002027 silica gel Inorganic materials 0.000 description 5
239000000126 substance Substances 0.000 description 5
238000005160 1H NMR spectroscopy Methods 0.000 description 4
239000011575 calcium Substances 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
239000012043 crude product Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
102000009310 vitamin D receptors Human genes 0.000 description 4
108050000156 vitamin D receptors Proteins 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
102000005962 receptors Human genes 0.000 description 3
108020003175 receptors Proteins 0.000 description 3
239000013558 reference substance Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
229920002307 Dextran Polymers 0.000 description 2
239000007818 Grignard reagent Substances 0.000 description 2
208000037147 Hypercalcaemia Diseases 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
208000012868 Overgrowth Diseases 0.000 description 2
229910019142 PO4 Inorganic materials 0.000 description 2
201000004681 Psoriasis Diseases 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
229910052791 calcium Inorganic materials 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
239000000969 carrier Substances 0.000 description 2
238000003776 cleavage reaction Methods 0.000 description 2
239000006071 cream Substances 0.000 description 2
238000010511 deprotection reaction Methods 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 2
230000000148 hypercalcaemia Effects 0.000 description 2
FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 2
230000004060 metabolic process Effects 0.000 description 2
239000002674 ointment Substances 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
239000010452 phosphate Substances 0.000 description 2
230000007017 scission Effects 0.000 description 2
125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
BNWCETAHAJSBFG-UHFFFAOYSA-N tert-butyl 2-bromoacetate Chemical compound CC(C)(C)OC(=O)CBr BNWCETAHAJSBFG-UHFFFAOYSA-N 0.000 description 2
230000000699 topical effect Effects 0.000 description 2
229940088594 vitamin Drugs 0.000 description 2
229930003231 vitamin Natural products 0.000 description 2
235000013343 vitamin Nutrition 0.000 description 2
239000011782 vitamin Substances 0.000 description 2
238000005406 washing Methods 0.000 description 2
YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 description 1
125000006545 (C1-C9) alkyl group Chemical group 0.000 description 1
AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
MJLVLHNXEOQASX-UHFFFAOYSA-N 2-bromo-3,3-dimethylbutanoic acid Chemical compound CC(C)(C)C(Br)C(O)=O MJLVLHNXEOQASX-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
206010006187 Breast cancer Diseases 0.000 description 1
208000026310 Breast neoplasm Diseases 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
206010009944 Colon cancer Diseases 0.000 description 1
239000004097 EU approved flavor enhancer Substances 0.000 description 1
241000287828 Gallus gallus Species 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
241000283973 Oryctolagus cuniculus Species 0.000 description 1
OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 1
229930003756 Vitamin B7 Natural products 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
230000002022 anti-cellular effect Effects 0.000 description 1
230000001028 anti-proliverative effect Effects 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
238000003556 assay Methods 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
102000023732 binding proteins Human genes 0.000 description 1
108091008324 binding proteins Proteins 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000012267 brine Substances 0.000 description 1
RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
244000309464 bull Species 0.000 description 1
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
LWQQLNNNIPYSNX-UROSTWAQSA-N calcipotriol Chemical compound C1([C@H](O)/C=C/[C@@H](C)[C@@H]2[C@]3(CCCC(/[C@@H]3CC2)=C\C=C\2C([C@@H](O)C[C@H](O)C/2)=C)C)CC1 LWQQLNNNIPYSNX-UROSTWAQSA-N 0.000 description 1
229960002882 calcipotriol Drugs 0.000 description 1
150000001668 calcitriol derivatives Chemical class 0.000 description 1
201000011510 cancer Diseases 0.000 description 1
239000002775 capsule Substances 0.000 description 1
125000002837 carbocyclic group Chemical group 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
150000001805 chlorine compounds Chemical group 0.000 description 1
238000011097 chromatography purification Methods 0.000 description 1
208000029742 colonic neoplasm Diseases 0.000 description 1
239000003086 colorant Substances 0.000 description 1
230000002860 competitive effect Effects 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
PBGGNZZGJIKBMJ-UHFFFAOYSA-N di(propan-2-yl)azanide Chemical compound CC(C)[N-]C(C)C PBGGNZZGJIKBMJ-UHFFFAOYSA-N 0.000 description 1
229940043279 diisopropylamine Drugs 0.000 description 1
238000007865 diluting Methods 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
238000010494 dissociation reaction Methods 0.000 description 1
230000005593 dissociations Effects 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000012467 final product Substances 0.000 description 1
235000019264 food flavour enhancer Nutrition 0.000 description 1
238000009472 formulation Methods 0.000 description 1
150000004795 grignard reagents Chemical class 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
230000033444 hydroxylation Effects 0.000 description 1
238000005805 hydroxylation reaction Methods 0.000 description 1
238000001802 infusion Methods 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
210000000936 intestine Anatomy 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
210000003734 kidney Anatomy 0.000 description 1
210000000265 leukocyte Anatomy 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical group [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
239000002207 metabolite Substances 0.000 description 1
210000004080 milk Anatomy 0.000 description 1
235000013336 milk Nutrition 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
GNWXVOQHLPBSSR-UHFFFAOYSA-N oxolane;toluene Chemical compound C1CCOC1.CC1=CC=CC=C1 GNWXVOQHLPBSSR-UHFFFAOYSA-N 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000003444 phase transfer catalyst Substances 0.000 description 1
238000007699 photoisomerization reaction Methods 0.000 description 1
239000006187 pill Substances 0.000 description 1
230000002062 proliferating effect Effects 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
239000012925 reference material Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
239000003270 steroid hormone Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000003826 tablet Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical class CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
238000005809 transesterification reaction Methods 0.000 description 1
238000012546 transfer Methods 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
235000011912 vitamin B7 Nutrition 0.000 description 1
239000011735 vitamin B7 Substances 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C401/00—Irradiation products of cholesterol or its derivatives; Vitamin D derivatives, 9,10-seco cyclopenta[a]phenanthrene or analogues obtained by chemical preparation without irradiation

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Steroid Compounds (AREA)

HU923157A 1990-04-06 1991-04-08 Process for producing 24-oxa derivatives belonging to vitamin d series and pharmaceutical compositions comprising same as active ingredient HUT62560A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE4011682A DE4011682A1 (de)	1990-04-06	1990-04-06	24-oxa-derivate in der vitamin d-reihe

Publications (2)

Publication Number	Publication Date
HU9203157D0 HU9203157D0 (en)	1992-12-28
HUT62560A true HUT62560A (en)	1993-05-28

Family

ID=6404190

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HU923157A HUT62560A (en)	1990-04-06	1991-04-08	Process for producing 24-oxa derivatives belonging to vitamin d series and pharmaceutical compositions comprising same as active ingredient

Country Status (13)

Country	Link
US (1)	US5292728A (pt)
EP (1)	EP0450743A1 (pt)
CN (1)	CN1055924A (pt)
AU (1)	AU7669491A (pt)
CA (1)	CA2080015A1 (pt)
DE (1)	DE4011682A1 (pt)
FI (1)	FI924478A7 (pt)
HU (1)	HUT62560A (pt)
IE (1)	IE911157A1 (pt)
IL (1)	IL97784A0 (pt)
PT (1)	PT97256A (pt)
WO (1)	WO1991015448A1 (pt)
ZA (1)	ZA912551B (pt)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB9017890D0 (en) *	1990-08-15	1990-09-26	Leo Pharm Prod Ltd	Chemical compounds i
US20040009958A1 (en) *	1991-01-08	2004-01-15	Bone Care International, Inc.	Methods for preparation and use of 1alpha,24(S)-dihydroxyvitamin D2
IL99368A (en) *	1991-09-02	1996-01-19	Teva Pharma	Preparations for the treatment of psoriasis and atopic dermatitis, which contain the result of xanthine
DE4220757A1 (de) *	1992-06-24	1994-01-05	Schering Ag	Derivate in der Vitamin D-Reihe mit Modifikationen in der 20-Position, Verfahren zu ihrer Herstellung, Zwischenprodukte für dieses Verfahren, diese Derivate enthaltende pharmazeutische Präparate sowie deren Verwendung zur Herstellung von Arzneimitteln
DE4221961A1 (de) *	1992-06-30	1994-01-05	Schering Ag	22-En-25-oxa-Derivate in der Vitamin D-Reihe, Verfahren zu ihrer Herstellung, diese Derivate enthaltenen pharmazeutische Präparate sowie deren Verwendung als Arzneimittel
DE69327906T2 (de) *	1992-10-16	2000-10-05	Chugai Seiyaku K.K., Tokio/Tokyo	Vitamin-d-derivat und verfahren zu seiner herstellung
GB9223061D0 (en) *	1992-11-04	1992-12-16	Leo Pharm Prod Ltd	Chemical compounds
US5449668A (en) *	1993-06-04	1995-09-12	Duphar International Research B.V.	Vitamin D compounds and method of preparing these compounds
US5401733A (en) *	1993-10-01	1995-03-28	Hoffmann-La Roche Inc.	Stable and active metabolites of 1,25-dihydroxy-16-ene-cholecalciferol
US5668037A (en) *	1995-10-06	1997-09-16	Micron Technology, Inc.	Method of forming a resistor and integrated circuitry having a resistor construction
US6087350A (en) *	1997-08-29	2000-07-11	University Of Pittsburgh Of The Commonwealth System Of Higher Education	Use of pretreatment chemicals to enhance efficacy of cytotoxic agents
ES2368824T3 (es) *	1998-03-27	2011-11-22	Oregon Health & Science University	Vitamina d y sus análogos en el tratamiento de tumores y otros desórdenes hiperproliferativos.
TWI329105B (en) *	2002-02-01	2010-08-21	Rigel Pharmaceuticals Inc	2,4-pyrimidinediamine compounds and their uses
WO2005012294A1 (en) *	2003-07-30	2005-02-10	Rigel Pharmaceuticals, Inc.	2,4-pyrimidinediamine compounds for use in the treatment or prevention of autoimmune diseases
JP2008543855A (ja)	2005-06-13	2008-12-04	ライジェルファーマシューティカルズ，インコーポレイテッド	変形性骨疾患を処置するための方法および組成物
ATE352714T1 (de) *	2005-06-17	2007-02-15	Magneti Marelli Powertrain Spa	Brennstoffeinspritzventil
JP5732471B2 (ja) *	2009-12-22	2015-06-10	レオファーマアクティーゼルスカブ	溶媒混合物およびビタミンｄ誘導体から成る医薬品組成物または類似体
CN111533712B (zh) *	2020-04-28	2023-06-09	南通华山药业有限公司	一种阿法骨化醇杂环衍生物及其制备方法和用途

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1990
- 1990-04-06 DE DE4011682A patent/DE4011682A1/de not_active Withdrawn
1991
- 1991-04-04 PT PT97256A patent/PT97256A/pt not_active Application Discontinuation
- 1991-04-05 ZA ZA912551A patent/ZA912551B/xx unknown
- 1991-04-06 CN CN91102857A patent/CN1055924A/zh active Pending
- 1991-04-07 IL IL97784A patent/IL97784A0/xx unknown
- 1991-04-08 IE IE115791A patent/IE911157A1/en unknown
- 1991-04-08 FI FI924478A patent/FI924478A7/fi not_active Application Discontinuation
- 1991-04-08 AU AU76694/91A patent/AU7669491A/en not_active Abandoned
- 1991-04-08 HU HU923157A patent/HUT62560A/hu unknown
- 1991-04-08 WO PCT/EP1991/000657 patent/WO1991015448A1/de not_active Ceased
- 1991-04-08 EP EP91250091A patent/EP0450743A1/de not_active Ceased
- 1991-04-08 CA CA002080015A patent/CA2080015A1/en not_active Abandoned
1992
- 1992-12-04 US US07/938,175 patent/US5292728A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
IE911157A1 (en)	1991-10-09
FI924478L (fi)	1992-10-05
AU7669491A (en)	1991-10-30
FI924478A0 (fi)	1992-10-05
DE4011682A1 (de)	1991-10-10
IL97784A0 (en)	1992-06-21
WO1991015448A1 (de)	1991-10-17
CA2080015A1 (en)	1991-10-07
PT97256A (pt)	1992-01-31
FI924478A7 (fi)	1992-10-05
CN1055924A (zh)	1991-11-06
ZA912551B (en)	1992-10-28
US5292728A (en)	1994-03-08
HU9203157D0 (en)	1992-12-28
EP0450743A1 (de)	1991-10-09

Legal Events

Date	Code	Title	Description
1994-11-28	DFC4	Cancellation of temporary protection due to refusal

Publication	Publication Date	Title
HUT62560A (en)	1993-05-28	Process for producing 24-oxa derivatives belonging to vitamin d series and pharmaceutical compositions comprising same as active ingredient
KR100301876B1 (ko)	2001-11-22	비타민d화합물및이들화합물의제조방법
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JP3207423B2 (ja)	2001-09-10	ビタミンｄ系列の２３−オキサ誘導体、その製造法、該誘導体を含有する製薬学的調剤ならびに医薬品としての該誘導体の使用
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AU707942B2 (en)	1999-07-22	New vitamin D derivatives with substituents at C-25, process for their production, intermediate products and use for the production of pharmaceutical agents
FI109996B (fi)	2002-11-15	Menetelmä terapeuttisesti käyttökelpoisen D-vitamiinisarjan 25-karboksyylihappojohdannaisten valmistamiseksi
HUT68263A (en)	1995-06-28	20-methyl-substituted vitamin d derivatives, process for their production, pharmaceutical compositions and intermediates
FR2634200A1 (fr)	1990-01-19	Nouveaux composes derives de la vitamine d, leur procede de preparation et compositions pharmaceutiques contenant ces composes
FR2630740A1 (fr)	1989-11-03	Composes derives de vitamine d3, procede pour les preparer et leur utilisation
HU210032B (en)	1995-01-30	Process for the production of 24-homo-d-vitamin derivatives and pharmaceutical compositions containing the same
FI109686B (fi)	2002-09-30	Menetelmä uusien D-vitamiinianalogien valmistamiseksi
CN101293894B (zh)	2011-04-06	制备2-亚丙基-19-去甲维生素d化合物的中间体
JPH09511224A (ja)	1997-11-11	ビタミンｄアミンおよびアミド誘導体
JP2908566B2 (ja)	1999-06-21	ビタミンｄ誘導体の皮膚科学的使用
JP2502931B2 (ja)	1996-05-29	ビタミンｄ３同族体
JPH06329696A (ja)	1994-11-29	ラクトン化合物及びその製造方法
JP3923090B2 (ja)	2007-05-30	ビタミンｄ３誘導体およびその製造法
FR2630739A1 (fr)	1989-11-03	Homologues a chaine laterale insaturee de vitamine d, compositions pharmaceutiques contenant ces composes, et leur utilisation
AU4320999A (en)	1999-12-13	Method for making hydroxy-25-ene-vitamin d compounds
US5721224A (en)	1998-02-24	Method of treating metabolic bone diseases with 18-nor-vitamin D compounds
EP0338796A2 (en)	1989-10-25	2-Substituted-2-cyclopentenones
JP3516715B2 (ja)	2004-04-05	２２−アルキル−２５，２６，２７−トリスノルビタミンｄ誘導体
EP1219599B1 (en)	2010-03-31	Vitamin d derivatives having substituents at the 2 alpha-position
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